


Practice Makes Perfect

by jhoom



Category: Supernatural
Genre: Bottom!Cas, College!AU, Friends to Lovers, M/M, Mutual Pining, dean is bi, dean/others - Freeform, roommate!AU, team switch (implied at the end), top!dean
Language: English
Status: Completed
Published: 2018-06-27
Updated: 2018-06-27
Packaged: 2019-05-29 11:48:19
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,993
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15072515
Author URL: https://archiveofourown.org/users/jhoom/pseuds/jhoom
Summary: Dean comes out as bi but feels a little too self-conscious about his lack of experience with men to put himself out on the dating scene... Good thing his best friend Cas is there to help him out.





	Practice Makes Perfect

**Author's Note:**

> So really this started as me posting a fic idea on tumblr and then my muse poking at me until I saw it through lol. 
> 
> Original post:  
>  _dean who’s just come out confessing to his best friend/roommate cas that he’s worried about dating guys because “it’s the same but it’s different, y’know? like the kissing and the date part i’m sure are about the same, but like… giving head’s a lot different, and that’s not even getting into sex.”_
> 
>  
> 
> _and cas casually offers to help him practice. cas, the fool, who completely thinks this is a friendly offer on his part and that there are no feelings involved. and dean, also a fool, thinks the same._
> 
>  
> 
> _spoiler: there are feelings involved, or at least there will be._
> 
>  
> 
> so here's everything i wrote on tumblr moved over into one spot on ao3 :) i did go through and make a few edits (the original was all lowercase, for example), but otherwise it's the same story that was posted to [my tumblr](http://jhoomwrites.tumblr.com).

Cas of course coaches Dean through giving a blowjob first. 

“You’ve gotten a blowjob before, right?” Cas asks, knowing the answer. They’ve been roommates going on six years, he’s seen and heard things. Plus he’s been good friends with some of dean’s exes. He knows.

“Yes, I’ve gotten a friggin blowjob,” Dean growls. How dare Cas imply otherwise.

“Then you have a good idea how a good blowjob should go.”

“Yeah but like… I don’t want to ruin it. I’m 24 friggin’ years old, I should know how to give head by now, right?” Cas gives him a look. “I just…” Dean blushes. “I don’t want to be some story some guy tells about a bad blowjob, y’know?”

“So let’s start with that.”

And just like that, Cas' pants are on the floor and Dean's on his knees in front of him. 

Dean is a very quick learner. It takes them both a few minutes to get into it. They’re not attracted to each other, remember? Or at least not in more than a passing acknowledgement that their best friend is hot. Cas is soft and then only half hard for the first five minutes and Dean’s about to die of mortification, but eventually something clicks and Cas is hard and leaking, and Dean’s eagerly taking him into his mouth. 

Cas gives him explicit instructions, gentle reminders on what to and not to do, encouragement when he does something particularly well. dean finds he’s super into being told what to do, and super into having a dick in his mouth, but he keeps both facts to himself. 

After asking permission, Cas gentle fists Dean’s hair and holds him steady so he can slowly fuck into his mouth. Not too deep, not too fast, just enough to give Dean some practice. That's the whole point, right?

“Dean,” Cas grunts. “I’m close.”

Dean hums in acknowledgement but makes no move to pull off. Cas warns him again, but Dean’s stubborn and won’t move.

O _kay,_  Cas thinks. I _guess he wants to swallow_. 

He does a great job, eagerly licking Cas clean. There’s a drop of come at the corner of his mouth that Cas has the urge to wipe away, but Dean does it before he can.

“I feel like I should return the favor,” Cas says, gesturing to the bulge in Dean’s pants. He's strangely pleased that Dean enjoyed himself.

“Nah, it’s cool. You were doing me a favor anyway. How’d I do?”

Cas gives a weak thumbs up. It was a good blowjob, though admittedly not the best he’s had. Very good for a beginner though. He doesn’t quite have the brainpower to voice any of that right now, but he promises himself he’ll let Dean know in more detail later. 

"Cool,” Dean says with a smile. “I’m gonna take a shower and take care of this. Wanna order pizza?”

Cas nods. He’s not up for cooking and he’s certainly not up for going out. Dean winks at him before he disappears down the hallway, already starting to unzip his jeans.

The next morning, Cas jerks off to the thought of Dean giving head. It’s unclear even in his own fantasy if he’s the one on the receiving end or not, but he thinks he’d enjoy watching if nothing else. 

~~And we all know Dean jerked off to the idea of giving Cas head in the Impala. It’s a common fantasy for him, getting road head, and now he’s got the experience of giving head, he wants to work it in. He admits it’s a little weird to imagine Cas as the one he’s blowing, but hey, whatever. It’s just practice.~~

~ ~ ~

Dean wouldn’t say he’s exclusively messing around with guys now, but he’s definitely more preoccupied with getting dick than pussy. Everything Cas told him gave him the confidence he needs and he feels like he’s been depriving himself all these years. More often than not when he hooks up with someone at a bar these days, it’s a guy.

Cas is happy to have helped and pleased to see Dean’s a lot more relaxed about things now than before. He may idly think about Dean when he jerks off, but only on occasion. He thinks of dean on his knees, looking up through long eyelashes, plush lips spread by a hard cock… It’s a pretty image, and though it might be weird to think of his best friend like that, he thinks Dean wouldn’t mind. 

~~Not that he says anything about it. No need to _actually_  make things weird, right?~~

He also on occasion wonders… does Dean  _always_  swallow? Was that a spur of the moment decision with Cas? Does he prefer to let his partner come on his face instead? Would he ever allow that, to spatter come amongst his freckles? Cas doesn’t see a good opportunity to actually ask (and what exactly would  _that_  opportunity even  _look_  like?), so he keeps his musings to himself.

~~Dean does in fact like to swallow _and_  let his partner come on his face. He’s really not picky… but he does often find himself comparing the taste to Cas, and he’s not sure what to do with the fact that he likes Cas’ come better than the random guys he picks up.~~

Overall Dean thinks his experiment with Cas was a huge success. He got the practice he wanted and it didn’t make things weird with Cas. The problem is… Dean’s nervous again. Handjobs and blowjobs are great and all, but he’s never let himself go farther than that with a guy. He’s nervous, ridiculously nervous, and it’s like he’s back to square one. He’s just… not comfortable going farther with a stranger, not when he’s never had sex with a guy before.

He got cas’ help before, but he’s reluctant to ask again. this is… more. Definitely more. He’s scared to bring it up… and he’s  _really_  scared by how much he  _wants_  his first time to be with Cas and only with Cas. 

What’s a boy to do? Proposition his best friend for sex or bite the bullet and fuck a stranger?

~ ~ ~

Dean can’t get the idea out of his head. What if he and Cas… 

He tries, he really does. He goes to bars, he drinks, he finds the prettiest, the hottest, the butchest guys he can but it always ends the same way… a blowjob or a handjob and maybe some fingering, but never sex. He just can’t.

~~In a moment of desperation, he even goes out with the intent of finding a guy with dark brown hair and bright blue eyes. It doesn’t help.~~

He gives up even pretending. It takes him forever to build up the courage, but he needs to talk to Cas.

“So uh… y’know how you uh… how you helped me before… with the… with the uhm…”

Even though cas finds his stammering adorable  ~~(and where did _that_  thought come from?)~~, he puts Dean out of his misery. “When you wanted me to help you learn how to give a satisfactory blowjob?”

Despite knowing each other since they were kids, Cas has  _never_  seen Dean blush this badly. A ~~gain, adorable.~~

“Yep,” Dean squeaks. “That. But uh… I need more help, I think? I’m just not… comfortable… having sex with some stranger. And like, I get that sex with a guy shouldn’t be all that different,” he adds in a rush. “Since I don’t think I want to bottom right now, y’know? But like… prepping someone just right… and making it sexy… I’ve only ever… I mean, I’ve done it to myself but like…” 

Dean wants to jump off a cliff at this point, but again Cas rescues him. 

“So you’d like to have penetrative sex with me?” he says slowly, careful to keep his tone neutral and face expressionless. Internally his body temperature’s skyrocketed, his heart’s pounding like crazy, and his cock is  _definitely_  on board. “As more practice?”

“Yes?”

Cas gives him a skeptical look. “You’ve had plenty of sex-”

“And I’d gotten plenty of blowjobs, too,” Dean snaps. “It’s different, and it just… makes me uncomfortable to try it with those strangers.” 

There is more left unsaid, the pointed reminder of Dean confessing how his first time having sex had not gone well. That it was awkward and embarrassing and he never did talk to Cassie much after that, further convincing Castiel that it really had  _not_  been a good experience for either. It took Dean almost a year of dating Lisa to be willing to try again, so Cas more than understands his reluctance now.

He holds up his hands in surrender. “You’re right. I’m glad you trust me with this and I’m more than happy to help in whatever way you need.”

Dean instantly relaxes and gives a half smile. “Really?” he asks, like he can’t believe his luck.

“I’ll admit it’s an odd request, but it’s certainly not one i’m opposed to. We’ve been best friends for years. I’m happy to help. Really.”

_Far too happy to help, in all honesty, but that is something i’ll have to deal with on my own…_

_~ ~ ~_

It would be weird to talk about where they’re going to do this, so they end up in Dean’s room because it’s closest. It’s even weirder to negotiate things like kissing and dirty talk, so they don’t say anything and don’t try either. 

It doesn’t matter, by the time they undress they’re both hard. 

Dean nudges Cas to the bed while he grabs some lube and a condom. He can’t quite look Cas in the eye as he settles between Cas’ legs and starts gently circling his hole. 

This at least is familiar. Cas can whisper instructions, praise, encouragement, the occasional reprimand. dean thrives under the attention, is pleased to see the slight flush on Cas’ face and is ridiculously proud when he draws out a yelp followed by a raspy moan from Cas. 

As Dean stretches Cas slowly, carefully, almost lovingly, Cas reminds him that he should distract his partner. Kisses or caresses can help them relax-

Dean swallows Cas’ cock in one swift motion and bobs his head back and forth, never once faltering to keep his hand moving. He’s pleased with the low moan Cas rewards him with, loves that Cas’ hands curl into his hair to guide him without ever really pushing or pulling him, and he can’t stop smiling with pride when Cas tells him: “Fuck, you’ve gotten a lot better at that…”

It takes a lot of effort on both their parts to keep Cas from coming too soon. Dean waits until Cas is practically begging to be fucked before he believes he’s stretched enough. 

“Fuck,” Dean hisses when he bottoms out. He’s now even more glad that he’s with Cas right now and not some stranger; he feels like he’s about to burst, and he blames it on his inexperience. 

~~Idiot.~~

“You’re doing great,” Cas whispers. “Just start slow and I’ll let you know when to speed up, okay?”

Dean gradually builds up a steady pace, one that both of them like. Dean’s not sure where to look, at Cas’ blissed out face or down to where he can watch his cock disappear in and out of his best friend. It’s weird, but he’s pretty sure being able to see the two together make it even better.

“Hand,” Cas urges. “Hand. My dick. I can’t… Close, but need-”

“Hey, I got you, don’t worry,” Dean says. It’s awkward trying to coordinate his hand and his hips, but he figures it out. Cas helps, his hand covering Dean’s and making sure he doesn’t falter. 

Cas is so beautiful when he comes, Dean can’t help it. He breaks the silent rule and leans down to kiss him. 

Possibly the best thing that happens: Cas kisses him back.

It’s rough and chaotic and too much teeth, off target, messy, but dean growls into the kiss and fucks wildly into Cas. This is good. This is really good, and he wants to chase that good feeling for as long as he can.

But then he comes too, and the kissing doesn’t stop. It loses that desperate edge and becomes slow, lazy kisses. Tender, as Cas pulls him even closer and Dean caresses Cas’ cheek, buries his hands in his hair. 

Neither wants it to stop, because they’re afraid if it stops bad things will happen. Like they’ll have to talk about this. or worse, it’ll never happen again.

They end up curled around each other, barely cleaned up. Dean (or maybe it was Cas) turns off the light. A blanket gets wrapped around them, and they both fall asleep to the sound of the other’s breathing. 

Tomorrow things might get weird, but at least they have tonight.

~ ~ ~

Cas doesn’t want to make things awkward (or rather,  _more_ awkward than necessary… he’s pretty sure it’ll be at least a  _little_  awkward for a couple days). Ss soon as he wakes up, he holds his breath to gauge how asleep Dean is. Once he thinks it’s safe, he carefully extracts himself from his best friend’s embrace and sneaks out of the room.

~~Of course the moment he moves, Dean wakes up, but he can’t bear to say anything, because that would mean hearing from Cas why he felt he had to sneak away… So yeah, Dean pretends to be asleep.~~

Things actually aren’t too bad once they actually brave leaving their rooms. Yeah, they don’t talk about… y’know… but they’re too good of friends not to recover from this. So they had really good sex that kinda derailed into a gentle make-out session and fell asleep in each other’s arms, so what? Could happen to anyone. 

As if they need to prove they’re good, they eagerly accept Charlie’s invitation to a bar. Dean loudly proclaims that he’s ready for a real hook up and Cas quietly admits that he probably should seek out a one night stand of his own. 

Because clearly this thing with Dean is going nowhere and he should nip any inconvenient feelings in the bud, right?

Right.

Dean dances with any even remotely pretty girl or attractive guy that looks his way. Cas is pretty sure he dances with half the bar, and despite his intention of doing the same, Cas can’t quite find the motivation. His heart’s just not in it, and he barely can bring himself to dance with Charlie when she asks.

After a while, Cas forces himself to stop watching Dean. Sure, he has a better idea why it pains him to see Dean in the arms of others, but that doesn’t mean he’s ready to- 

His musings are interrupted by the loud clattering of two beer bottles being placed on the table in front of him. 

“Mind if i buy you a drink?” Dean asks. Cas is momentarily stunned. He knows that smile, that flirty tone, but he’s never had it directed at  _him_  before.

Not quite able to speak, he silently accepts one of the beers and chugs half of it in the hopes that it’ll clear his mind. It doesn’t, but oh well.

“So, i was thinking,” Dean says slowly, looking at the table except when his eyes flash up through his lashes to Cas. “You’ve been a lot of help. A great teacher, best I ever had.”

 _Don’t remind me, C_ as thinks remorsefully. He can’t quite stomach imagining Dean putting his “new skills” to the test with other men. “You’re welcome,” is what he manages to say out loud. Somehow.

Dean smiles, but some of that flirtiness is gone. There’s something nervous underneath the surface, and now Cas is starting to get worried. 

“So, like I said,” Dean continues, his hand absentmindedly peeling the label of his beer bottle, “I’ve been thinking. and i thought… y’know, there are a lot of things left I kinda wanna… try out. Like yeah, I can give head and fuck a guy, but like… what if I wanna bottom? Or try rimming? Shower sex with a guy’s probably different than with a chick, right? Same with car sex and 69 and uh… and y’know, I’ve never had a  _boyfriend_  before, and I honestly can’t think of a guy I’d rather try that out with than you.”

Cas’ brain fizzled out about halfway through dean’s speech, but eventually it catches up. He nearly falls out of his seat when he hears Dean say the word “boyfriend” but something desperate, some mix of eagerness and relief and joy keeps him steady enough to say:

“I’d like that very much, dean.” And somehow he recovers enough to smile and add, “I’m sure you could use a lot of practice.”

“Tons,” Dean agrees easily, his grin blinding and making Cas feel fuzzy all over again. “You’re gonna have to work with me years before I get it right.”

Cas gives an exaggerated sigh. “Probably. But as your best friend, I really feel like it’s my duty.”

“Absolutely.”

~~And yes, they totally end up having sex in the bathroom five minutes later.~~

\- fin - 

* * *

**epilogue/bonus scene:**

*after years of dating*

 **dean:**  cas, thank you for teaching me how to blow, fuck, and give guys mindblowing orgasms.

 **cas:** no problem. it’s not like i haven’t benefited from the process.

 **dean:** and thanks for teaching me how to date a guy. i really appreciate it.

 **cas, eyes narrowing:** … you’re welcome?

 **dean:** it’s just that now i feel like i’m ready to move onto the next step. you’ve taught me everything i need to know about dating a guy, and i was hoping you’d do me a huge favor and help me learn one more thing.

 **cas:** …. uh

 **dean, getting on one knee and holding up a ring:** would you help me learn how to be a good husband to my husband?

 **cas, with tears in his eyes:** you idiot. yes i will.


End file.
